Monoazo dyestuffs



Patented Feb. 9, 1937 UNITED STATES PATENT OFFICE,

MONOAZO DYESTUFFS Richard Fleischhauer, Frankfort-on-the-Main, Fechenheim, and Carl Theo Schultis, Bergen, near Hanau-on-the-Main, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing.

Application May 5, 1936, Serial No.

77,992. In Germany May 9, 1935 4 Claims.

The present invention relates to valuable new monoazo dyestufis, more particularly to those of the general formula:

of the benzene or naphthalene series. The new dyestuffs are obtained by combining the diazo compounds of aromatic amines of the following formula:

(wherein R1 and R2 have the above said signification) with acylated derivatives of peri-aminonaphthol-disulfonic acids containing the radical of an aryloxy fatty acid.

Diazo components of the above species have been already combined with a benzoylaminonaphthol-disulfonic acid (see U. S. A. Patent No. 1,113,622). The present new dyestuffs are distinguished in a surprising manner from those products by better fastness to perspiration besides Very good fastness to fulling. Moreover the new products yield substantially more yellowish and very clear red shades of good fastness to washing, fulling and light, which shades are required by the dyers in many cases.

The diazo components used for the present process may be obtained for example by condensing the corresponding secondary amines with a nitrobenzoyl chloride which may contain further substituents in its benzene nucleus, and by reducing the condensation products obtained.

In order to further illustrate our invention the following examples are given, the parts being by weight and all temperatures in centigrade degrees; but we wish it however to be understood that our invention is not limited to the examples given, nor to the exact conditions stated therein.

Example 1 29 parts of p-amino-benzoyl-ethyl-u-naphthylamine are diazotized in the usual manner. The diazo solution obtained is allowed to run into a solution of 49 parts of l-(2'-chlorophenoxyacetylamino)-8-naphtho1-4,6-disulfonic acid containing an excess of sodium carbonate. When the combination is complete the dyestufi formed of the following formula:

OH NHCOCHzO HOaS OaH

is isolated and dried. It forms a red powder, soluble in water, dyeing wool and silk Very bright red shades of excellent fastness to washing and very good fastness to perspiration and light.

By employing m-aminobenzoyl-ethyl-u-naphthylamine in the above example bright scarlet shades of equal properties are obtained. By employing as combining components l-phenoxyacetylamino-8-naphthol-4,6-disulfonic acid or substituted derivatives thereof containing in the phenoxy residue other substituents such as for example one or more methyl, methoxy or nitro groups or several halogen atoms, dyestuffs are obtained of somewhat different shades, but of equal good fastness properties.

In an analogous manner the residues of other aryloxy fatty acids such as for example phenoxypropionic acid, naphthoxy-acetic acids and substituted derivatives thereof may be introduced into the molecule of the combining components.

Example 2 A diazo solution prepared in the usual manner by starting from 30 parts of p-aminobenzoyl-dicyclohexyl-amine is combined with the solution of 49 parts of 1-(2'-chloro-phenoxyacetyl-amino)-8-naphthol-4,6-disulfonic acid in the presence of sodium carbonate.

The dyestufi formed of the following formula:

is isolated and dried. It is a red powder, soluble in water with a red color and dyeing wool or silk bright red shades of very good fastnessto rum i'ng, light and perspiration. By employing the. corresponding mor o-amino compoundsinstead of the p-amino-benzoyl compound, dyeings of equal'fastness. but more yellowish red shades, areiobtained.

Similar red dyestuffs of likewisevery good fast- CHzOHzGHaOHn CH'CHIOHIOHI ness propertiesare obtained by replacing the above said diazo components for example by the corresponding amounts of amino-benzoyl-cyclohexyl-phenyl-amines, amino-benzoyl -diphenylamines, aminobenzoyl benzyl phenylamines,

amino-benzoyl-carb'azoles and other amino compounds of similar constitution.

24,'8 parts oi p afninobenzoyl-di-n-buty1ani line are diazotized in the usual manner. The diazo solution obtained is allowed to run into a solution: of 49 parts oi 1,-(2-ch1oropheno xy acetylamino) 8 naphthol 4,6 disulfonic acid containing an excess oi sodium carbonate. Thedyestufi formed of the formula:

ch1oro-5-amino-benzoyl-di-(n-butyD -amine and similar compounds.

/ OH Nncoomo Erampled 2ij8 parts {of ""m-ami'nob enzoyl -di-n-butylamine are dia'aotiz'edin the usual manner. The diazo solution obtained is allowed to run into a solution of d'l parts of 1-(2'emethyl-phenoxyacetylamino) -8-naphthol-4,6-disulfonic acid 'con tain The dyestufl.

ing an excessof sodium carbonate. formed of the formula:

on nnooomo SOIH is isolated and dried. Itiorms a red powder,' soluble in water,:dyeing wool and silk bright red shades'of very good fa'stness towashingyfulling, light, perspiration and sea-water. A dyestufi of similar properties is obtained by employing 1-(4-methyl-phenoxyacetylamino-8- naphthol-4,6-disulfonic acid.

Example 5 30,2 parts of p-aminobenzoyl-N-benzylaniline are diazotized in theus ualymanner and combined with 47'" parts "of 1-(4j' methybphenoxwaoetylpresence'of sodium carbonate. The dyestufiob I OH NHCOOHIO omomomog,

cmcmcmcH;

di-isobutylamine, aminobenzoyl-znethyl isohexylamine, aminobenzoyl methyl-isoamylariiine, 3; amino 4-methyl-benzoyl+di cyclohexyl amine, 2

- OaH tained of the formula:

.HOaS

is isolated and'driedi "-It form'sa red powdem soluble in waterwith a :red color, dyeing woolgand washing, light and perspiration A dyestuffofsimilar properties is obtained by employing: 1% 2f :me'tliyl phenoxyacetylamino) 8-naphthol-4;6 disulion1c" acid;

silk very charred-shades ofve'ry good'fastness'to 7 .is isolated and dried. It forms a red powder,

Example 6 0H NBC 0 01110 0311 is isolated and dried. It forms a red powder, soluble in water with a red color, dyeing wool and silk very bright red shades of very good fastness to washing, light and perspiration.

Example 7 30 parts of m-aminobenzoyl-dicyclo-hexylamine are diazotized in the usual manner. The diazo solution obtained is allowed to run into a solution of 49 parts of 1-(2'-chloro-phenoxyacetsoluble in water with a red color, dyeing Wool and silk bright red shades, fast to fulling, light and perspiration.

We claim:

1. The monoazo dyestuffs of the general formula:

wherein R1 and R2 stand for a member of the group consisting of an aliphatic, cycloaliphatic, phenyl, naphthyl and benzyl radical or R1 and R2 form with N a heterocyclic ring, one of the Zs stands for hydrogen and the other one for a sulfonic acid group, and aryl means a radicle of the group consisting of the radicals of henzene and naphthalene series, which dyestuffs yield on fibers, especially wool or silk, bright red shades of very good fastness to washing, fulling, light and perspiration.

ylamino)-8-naphtho1-3,6-disulfonic acid con- 2. The mono azo dyestuff of the formula:

OH NHOOOHnO CHaCHaCHzCHn I I CHaCHzCHzCHz taining an excess of sodium carbonate. When the combination is complete the dyestufi formed of the formula:

HOaS

SOaH which dyestuii represents a red powder, soluble in water, dyeing wool bright red shades of very good fastness to fulling, light and perspiration.

H1 H1 5- 0H NHoocmo H=o /CH 01 H: Illa H H /N-C0 H038 2 Z l\ SOsH HnC CH 0-0 A, 3. The mono azo dyestufi of the formula:

OH NHCOOHzO CHs omomomom /N=N CHaCHaCHzOHi which dyestufi represents a red powder, soluble in water, dyeing wool and silk bright red shades of very good fastness to washing, fulling, light, per- H H spiration and sea-water.

4. The mono azo dyestuff of the formula: on NHOOOHaO 1110 CH 01 H1 HI H N-C H035 sonz (J-(J which dyestufi represents a red powder, soluble in water, dyeing wool and silk bright red shades,

fast to fulling, light and perspiration. -f RICHARD FLEISCHHAUER. Ha H: CARL THEO SCHULTIS. 

